4-Methoxyphenol → HCID 86690883, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-fluoro-4-iodo-6-methylphenyl)ethanone (30-4, 1.1 g, 4.0 mmol), K3PO4 (1.7 g, 8.0 mmol), 4-methoxy-phenol (0.60 g, 4.8 mmol) in toluene (20 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (51 mg, 0.12 mmol), Pd(OAc)2 (38 mg, 0.08 mmol). The reaction was heated at 100° C. overnight under N2. The solution was cooled to room temperature and filtered through a small pad of diatomaceous earth. The cake was washed with ethyl acetate (50 mL) and combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(2-fluoro-4-(4-methoxyphenoxy)-6-methylphenyl)ethanone (0.47 g, 1.7 mmol) as yellow oil in 43% yield: 1H NMR (500 MHz, CDCl3) δ 6.97 (m, 2 H), 6.90 (m, 2 H), 6.54 (s, 1 H), 6.42 (m, 1 H), 3.80 (s, 3 H), 2.50 (d, J=4.1 Hz, 3 H), 2.30 (s, 3 H). ESI-MS: m/z 275.0 (M+H)+.

Provenance & Evidence